Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H23FN4O3.CH4O3S |
| Molecular Weight | 482.526 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CC1=C(N2C[C@@H](N)C3(CC3)C2)C(F)=C(N)C4=C1N(C=C(C(O)=O)C4=O)C5CC5
InChI
InChIKey=QCRMQMNCFYYEFX-UTONKHPSSA-N
InChI=1S/C20H23FN4O3.CH4O3S/c1-9-16-13(18(26)11(19(27)28)6-25(16)10-2-3-10)15(23)14(21)17(9)24-7-12(22)20(8-24)4-5-20;1-5(2,3)4/h6,10,12H,2-5,7-8,22-23H2,1H3,(H,27,28);1H3,(H,2,3,4)/t12-;/m1./s1
| Molecular Formula | C20H23FN4O3 |
| Molecular Weight | 386.42 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including http://adisinsight.springer.com/drugs/800006301 | http://www.ncbi.nlm.nih.gov/pubmed/12957636 | https://www.ncbi.nlm.nih.gov/pubmed/15608441
Curator's Comment: description was created based on several sources, including http://adisinsight.springer.com/drugs/800006301 | http://www.ncbi.nlm.nih.gov/pubmed/12957636 | https://www.ncbi.nlm.nih.gov/pubmed/15608441
Olamufloxacin (HSR-903) is an oral fluoroquinolone antimicrobial agent which has been reported to have a potent activity against respiratory pathogens, such as Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, Klebsiella pneumoniae, Staphylococcus aureus, Chlamydia spp. and Legionella spp., as well. Olamufloxacin inhibits DNA gyrase from the susceptible and resistant bacterial strains. It has been shown that olamufloxacin possesses a more potent antibacterial activity against potential respiratory pathogens compared with other quinolone derivatives. An oral formulation of olamufloxacin was undergoing phase III for Bacterial infections in Japan (Discontinued).
CNS Activity
Curator's Comment: Known to be CNS penetrant in rats. Human data is not available. Tissue-to-plasma concentration ratio (Kp) in brain is extremely low, 0.11, demonstrating very poor distribution to the brain compared with other tissues. The blood-brain barrier permeability coefficient of [14C]Olamufloxacin ([14C]HSR-903) at a very low concentration (5 μm) was 10.5 μl/min/g. When the concentration of HSR-903 was increased to 20 or 50 mM, the permeability coefficient was increased 3- to 4-fold.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2311224 |
20.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
|||
| Curative | Unknown Approved UseUnknown |
|||
| Curative | Unknown Approved UseUnknown |
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| Curative | Unknown Approved UseUnknown |
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| Curative | Unknown Approved UseUnknown |
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| Curative | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro and in vivo antichlamydial activities of HSR-903, a new fluoroquinolone antibiotic. | 1997 Apr |
|
| In-vitro antimicrobial activity of HSR-903, a new fluoroquinolone, against clinical isolates of Klebsiella pneumoniae and Enterobacter cloacae with fluoroquinolone resistance-associated amino acid alterations in GyrA and ParC. | 1997 Dec |
|
| In vitro activity of HSR-903, a new quinolone. | 1997 Jun |
|
| In vivo activity of HSR-903, a new fluoroquinolone, against respiratory pathogens. | 1998 Apr |
|
| Carrier-mediated lung distribution of HSR-903, a new quinolone antibacterial agent. | 1999 Apr |
|
| Comparative in vitro antimicrobial activities of the newly synthesized quinolone HSR-903, sitafloxacin (DU-6859a), gatifloxacin (AM-1155), and levofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex. | 1999 Dec |
|
| Efflux transport of a new quinolone antibacterial agent, HSR-903, across the blood-brain barrier. | 1999 Jul |
|
| Effect of HSR-903, a new fluoroquinolone, on the concentration of theophylline in serum. | 1999 Jun |
|
| The in vivo activity of olamufloxacin (HSR-903) in systemic and urinary tract infections in mice. | 2001 Jul |
|
| Susceptibility of Yersinia pestis to novel and conventional antimicrobial agents. | 2003 Aug |
|
| In vitro and in vivo activity of olamufloxacin (HSR-903) against Legionella spp. | 2003 Dec |
Patents
| Substance Class |
Chemical
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